CHAPTER 8: Question 10

 

Simple Answers

 a)

1,1-Disubstituted: Both conformations are achiral, which is more stable (ie. the minimum energy conformation) depends upon the relative sizes of R and R'.

 

1,2-Cis-disubstituted: Both conformations are chiral, which is more stable (ie. the minimum energy conformation) depends upon the relative sizes of R and R'.

 

1,2-Trans-disubstituted: Both conformations are chiral, the conformation with both substituents in equatorial positions will be the minimum energy conformation.

 

1,3-Cis-disubstituted: Both conformations are chiral, the conformation with both substituents in equatorial positions will be the minimum energy conformation.

 

1,3-Trans-disubstituted: Both conformations are chiral, which is more stable (ie. the minimum energy conformation) depends upon the relative sizes of R and R'.

 

1,4-Cis-disubstituted: Both conformations are achiral, which is more stable (ie. the minimum energy conformation) depends upon the relative sizes of R and R'.

 

1,4-Trans-disubstituted: Both conformations are achiral, the conformation with both substituents in equatorial positions will be the minimum energy conformation.


b) The structures of the minimum energy conformation of the 12 possible isomers is shown below.

view 3D explanation of the answer to question 10

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